


You Never Know Unless You Try

by spntvdtwhp



Category: Teen Wolf (TV)
Genre: Blow Jobs, F/M, Gay Sex, M/M, might be a bit of a slow burn
Language: English
Status: Completed
Published: 2020-03-14
Updated: 2020-03-26
Packaged: 2021-02-28 23:35:41
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 9,805
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23135515
Author URL: https://archiveofourown.org/users/spntvdtwhp/pseuds/spntvdtwhp
Summary: Stiles Stilinski has been in love with Jackson Whittemore since forever. He has always played it like he didn't like him, but that is starting to get old. Stiles knows Jackson will never feel the same so he tries to cover his feelings in other ways. But what if Jackson has feeling for Stiles just the same?
Relationships: Aiden/Lydia Martin, Ethan/Danny Mahealani, Isaac Lahey/Scott McCall, Stiles Stilinski/Jackson Whittemore, Vernon Boyd/Erica Reyes
Comments: 20
Kudos: 173





	1. Chapter 1

Stiles Stilinski is a quirky, clumbsy, and very intelligent guy. Like he was really smart, so smart that one day he knew that he would be a great asset to the FBI, if that is what he decided to do. Right now, though, Stiles was 17 years old at Beacon Hills High school and completely and utterly in love with none other than his nemesis, Jackson FUCKING Whittemore. 

That is why at this very moment, sitting across the cafeteria he was practically drooling at the sight of the lacrosse player as he was laughing at something Danny had said. Scott, Stile’s best friend is the only reason Jackson had not found out about Stile’s little, oh who was he kidding, GINORMOUS crush on him. When it came to Jackson Stiles wasn’t so smart. For instance, right now Scott had already followed Stile’s line of sight and was quickly gaining the other boys attention before anyone else noticed where Stiles was looking. Scott was always making sure Stiles was not too obvious about his crush on the other boy. Scott is the only one who knew about Stile’s major crush on Jackson. 

Stiles focused his attention back on his group of friends in front of him. They were all laughing at a joke Isaac had just told. Isaac was sitting next to Scott, holding his hand. They had become an item after the loss of Allison. They both had been there to comfort one another and found just what they needed in each other. Erika and Boyd were sitting across the table from Stiles. The two have been together since Kindergarten, when Erika had wanted to get to the slide first and pushed a startled Boyd out of the way by showing her feminine power. They’d been in love ever since. Now, Lydia had joined their friend group after her and Jackson’s “mutual” breakup. The power couple had just decided they weren’t the right fit. Which was just as well for Lydia when the twins Ethan and Aiden had shown up. Lydia knew she had to have one and went for the straight one, “obviously”. Aiden and her have been dating ever since. That left Stiles, the only one at the table during lunch without a lover. Not that that bothered him that much he was so genuinely happy for his friends, but that didn’t mean it didn’t suck seeing them all happy when he was in love with a boy, he knew he could never have. 

He found himself zoning out again in that moment, he could not help himself, Jackson was just so fucking hot. Him and his stupid perfect jawline that could cut glass and his perfectly sculpted abs and his piercing blue eyes that Stiles could always get lost in without realizing it. Stiles had always tried to disguise his crush on Jackson by putting all his infatuation on to Lydia, especially when they were younger. He did not need anyone finding out his feelings and using it against him, especially the older boy. Not that it matters now, Stiles had come out as gay (even if it was only like a month ago) and all his friends and his father had supported him. He couldn’t be happier, except if Jackson had only liked him too. 

Stiles tried to drown out the fact that he would never get to be with the boy he so longed to be with by going to the only gay club in town, Jungle. Tonight, was one of those nights! Since his friends had found out that Stiles was into guys they planned this night out so they could all hang out and support Stiles. Erika was really excited about Stiles maybe finding a mans. Before that though, Lydia decided Stiles needed a whole new outfit, especially if they were going to the club. What Lydia didn’t know is that Stiles had had success at that bar before she knew anything, but he wasn’t going to hurt her feelings and deny her a shopping trip. 

The bell rings, letting them know lunch is over, shaking Stiles out of his thoughts. He turns to Lydia and asks, 

“Where do you want to meet after school? Are we taking your car or Roscoe?” Lydia looked at him and like he should already know the answer and stated, **“I will pick you up from your house 30 minutes after school has ended. You better be ready.”**

****

****

Stiles was already excited about the prospect of going shopping with Lydia. He liked his style but he knew she had a great sense of fashion that would help him amp up his tastes. He smiled excitedly and started walking out of the cafeteria with a wave to Lydia as he headed to his next class. 


	2. Chapter 2

The rest of school flew by for Stiles. He spent his class after lunch staring at the back of Jackson’s head and fantasizing about what they could be doing, they were in Biology after all. In his last class of the day he was just too excited about the prospect of going shopping with Lydia that he could barely wait. As he was driving home now, he was wondering what exactly the experience would be like. Would Lydia make him try on a million different outfits, were they going to gossip, what kind of clothes would she pick for him, would she let him get some more graphic tees?? His mind was whirling with options (though he knew the last one would be a hard no). 

When he pulled into the drive he quickly jumped out of Roscoe, being careful not to slam the jeep’s door and ran inside. Once he got up to his room Stiles knew he needed to take a quick shower because he didn’t think he would have time to get ready for the club after his shopping date with Lyds. Stiles hopped into the shower meaning to be quick, but as soon as the hot water hit him his mind started to wander. Images of Jackson’s bright eyes and brilliant abs filled his mind. Stiles checked his phone just to make sure, he shrugged he still had 20 minutes before Lydia was supposed to be there. He got back to the problem at hand. His mind filled with images of Jackson soon turned to fantasy. Stiles dick was standing fully erect as he imagined Jackson having him pushed up against a locker kissing him hard. Then Jackson would pull back and look at him with that signature smirk before pushing Stiles to his knees. Stiles would pull out Jacksons thick cock and lick at the head before taking him into his mouth. Jackson’s hands would fly to his hair and hold Stiles mouth on his dick for a couple seconds longer. Stiles would sit back on his heels and look up at Jackson through his lashes silently giving Jackson permission to do as he pleases. As Jackson face fucked him in his fantasy, Stiles hand was moving quickly up and down his own shaft in the shower. It wasn’t long before Stiles was erupting over the shower wall. It took a minute for Stiles to get out of his post-orgasmic haze. He slowly went through the motions of cleaning himself. When he stepped out of the shower, he checked his phone and only had 5 minutes until Lydia was supposed to be there. Stiles scrambled to dry himself off and he quickly threw on something to wear. By the time he was finished his phone is ringing signaling to him Lydia was outside. 

Stiles grabbed his phone and his keys and flew down stair as to not make Lydia wait any longer. When he hopped in the passenger seat of her silver Prius, Lydia looked at him in disdain and rolled her eyes. Oh, come on he couldn’t look that bad! Stiles pulled down the little mirror so he could look at himself, his hair was a little wild but that was a normal for him. Lydia gave a small smile before stating, 

“Stiles, I wasn’t judging your hair, I was judging your clothes. This is why you need me to take you shopping!” Stiles put on a face of offense before looking Lydia straight in the eyes and saying, 

“Batman is cool and there is no way you can convince me any different and I will not stop telling the world.” Lydia just rolled her eyes fondly at Stiles and they started there 20-minute ride to the mall. When they finally arrived at the mall it was around 4:30 so they still had a few hours before they were supposed to meet the gang at Jungle. Stiles was nervously excited about what was going to happen in the next hours. Lydia though seemed to be on laser focus. She had a list in her hand and was already pulling him into a store to try stuff on. Stiles doesn’t know how many stores they go to, or how much Lydia made him try on, he seemed to have lost all track of time. He did notice that Lydia seemed to be texting a lot, he figured she was just texting Aiden and didn’t question it. All he knows is he kept telling Lydia he couldn’t afford all these clothes and she said that it was okay this was her gift to him. She practically bought him a whole new wardrobe. Lydia also decided that she would be picking out all of his outfits for school and she was choosing which outfit he was going to wear that night. When Stiles finally checked his phone, it was already 7:30 he could not believe they had been shopping for so long. Stiles stomach growled, and Lydia knew they needed to get a bite to eat before they went and met everyone at the club. They stopped at the Food Court and got something to eat quickly. Lydia had Stiles put on her favorite outfit they had got that day before they left for the club. When Stiles emerged from the bathroom Lydia was grinning from ear to ear obviously proud of herself. Stiles looked hot. He was in a tight pair of black skinny jeans, a white V neck shirt that accentuated his lean figure, and black converse to pull the outfit together.   
Stiles and Lydia left the mall and started their drive to Jungle. Stiles was excited for all his friends to be out with him tonight. He knew it was going to be a great time. When they pulled into the parking lot of the club Stiles was giddy with excitement. He hopped out of Lydia’s car super-fast and ungraceful. Lydia rolled her eyes as she got out of the car. She stopped him and mussed up his hair to her liking. Stiles looked in the mirror on the side of the car and damn he looked like he had sex hair. He looked so good he was definitely getting some tonight. Lydia gave him one last glance over before nodding her head approvingly saying, 

“Okay, let’s go have some fun!” Stiles grinned widely and they started towards the door.

**Notes for the Chapter:**

> Again, this is my first time writing so go easy on me...! I am really nervous, I hope I did alright with the shower scene. Let me know :)


	3. Chapter 3

**Summary for the Chapter:**

> Jackson's POV

Jackson Whittemore is rich, popular, great at lacrosse, and handsome as fuck. Yeah he knows he is. He can do anything he wants. Girls want him, boys want him, what can he say he’s everyone’s type. Everyone except a certain brown eyed boy he wishes would just love him. 

Stiles was sexy as hell and Jackson tries to ignore him every chance he gets because he knows the other boy will never want him and he can’t have anyone know about his crush. The only one who even knows he has the hots for Stiles is his best friends Danny. Danny has been by his side since he was born. They grew up together. When Jackson came out as bi after he and Lydia and he had broken up Danny had been supportive and said he knew all along. Danny was the best friend anyone can ask for, especially Jackson because he was an asshole and everyone knew it, even him. 

It was moments like these that Jackson really appreciated Danny because he was caught up in staring at Stiles across the cafeteria. Stiles always seemed to be having a good time with his friends laughing and joking with them, but when Jackson was looking at him now, he seemed to be lost in thought. Jackson loved seeing Stiles like this. It looked like all the gears in his head were turning and he looked completely content, Jackson knows Stiles is smart so seeing him like this always makes Jackson smile fondly. Sure, Stiles is sexy with his milky white skin, his amber eyes, his hair that always makes it look like he just got done having sex, and his moles. Don’t even get Jackson started on his moles Jackson wants to take his time and play connect the dots with his tongue on Stiles moles. Danny snapped his fingers in Jackson’s face bringing him back to earth with a jump. Danny laughs and share a knowing look with his boyfriend Ethan. Danny and Ethan have been dating since Ethan and his twin brother Aiden moved to Beacon Hills. A couple other kids from the lacrosse team were sitting with them at the table. They seemed to all want to sit at his table since he was the captain, well, all except Stiles, Stiles best friend Scott, Scott’s boyfriend, and Aiden (but Aiden didn’t sit their because he ate with Lydia). 

Jackson never really knew why the other boy never fawned over him like everyone else did. He wanted him too, obviously, but that never came. Jackson didn’t understand how he could be everyone’s type but Stiles. It was so frustrating to him. Danny always laughed at him and told him that maybe he would actually have to work for something for once instead of having it just fall into his lap. That scared Jackson, because what if he tried to woo Stiles and Stiles rejected him. He couldn’t take that kind of abandonment again. That’s why he both desperately wanted Stiles, but also was okay with watching from afar so he wouldn’t get broken. Plus, Stiles wasn’t in a relationship or with anyone else so Jackson didn’t have any reason to be upset, he could just be content with seeing Stiles. 

The bell rang and Jackson snapped back into focus, damn he needed to stop doing that. He turned to Danny who was looking at him expectantly,   
“I’m sorry, what?” he asks. “I didn’t catch what you said.” Danny laughed and shook his head, 

“I asked if you wanted to go to Jungle tonight with Ethan and me? We can have a lot of fun and maybe you can find someone to get your mind off you know who.” Danny winked at him. Jackson scoffed and shot Danny his signature sneer, 

“I don’t need any help in that department. But yeah sounds fun, when should I meet you there?” Danny rolled his eyes, 

“Yeah okay, Mr. ‘I’m everyone’s type’, we will see you there at 8:00.” Jackson smiled at his best friend and nodded his head in goodbye before heading to his next class, Biology. Jackson always got nervous when it came to this class because it was one out of the two classes he shared with Stiles. He put on a mask so no one could see how nervous he was, but he still felt the butterflies in his stomach. It also didn’t help that Stiles sat right behind him. Jackson couldn’t even concentrate on the lesson with Stiles so close to him, he started thinking about all the extra work they could do with their knowledge of biology. Jackson wanted to wait in the locker room after practice, after everyone had gone home, everyone but Stiles that is. Jackson would walk up to Stiles in only his gray sweatpants and see a shudder go down the other boys spine as his eyes roamed over Jackson’s body. Jackson would smirk and say ‘see something you like?’ in a seductive tone. He would watch as a blush formed on Stiles cheeks before stepping forward his eyes glinting as Stiles steps back until his back is flush against the lockers. Jackson would lean in and kiss Stiles slowly at first and then harder and with more passion asking for entrance with his tongue, which Stiles would grant him access with a moan of pleasure. Jackson would move on to Stiles neck licking and sucking while listening to the other boy whine as he tried to gain some sort of friction. Shit, Jackson jumps back into reality as someone dropped something in class. This is not good at all Jackson had a hard on in the middle of class. He willed his erection down as there was only a couple minutes until the end of class and then he could go home as this was his last class of the day. 

When the bell rang Jackson jumped into his Porsche and sped home. When Jackson finally got into his room he flopped down into his bed and jerked off vigorously to his fantasy from before. He came within a couple minutes, which normally would be odd for him, but since he started fantasizing about Stiles it just takes him over so quickly. Jackson suddenly feels exhausted, knowing he will need energy for the club tonight he decides he needs a nap. He goes to his bathroom and cleans himself off before, changing into a pair of sweatpants and setting his alarm for six. 

When Jackson wakes from his alarm, he wants to hit snooze, but knows he needs some time to get rid of his grogginess and get ready to go. Jackson lays in bed on his phone for about 30 minutes before he decides he needs to get up and take a shower. He takes his time in the shower making sure he is very clean before he finally shuts off the water and steps out to dry himself off. He wraps his towel on his waist before walking back into his room to decide what to wear. He decided on a white t-shirt that hugged his form nicely with his black leather jacket on top, a pair of blue jeans that show off his ass, and his favorite pair of black vans. He went back to the bathroom a gelled his hair to its pristine style. He looked in the mirror and gave himself a satisfied grin, oh hell yeah, he looked good. He was definitely getting some tonight.

**Notes for the Chapter:**

> Thank you for reading! I hope you enjoyed hearing Jackson's side of things. :)


	4. Chapter 4

**Summary for the Chapter:**

> Lydia hatches a plan

Lydia had had enough she was so tired of the fact that Stiles and Jackson were clearly in love with each other but they both refused to admit it, and they were both so oblivious. She can tell they both think they are sly and think no one can figure them out, but she isn’t stupid. She decided that she needed to step in and give them a little push towards one another. So, she texts Danny. 

Lydia: Okay, I’m so over this drooling. I have a plan, and I need your help. 

Danny: Oh thank goodness! I can’t stand it anymore... what’s the plan?? 

Lydia looked up to meet Danny’s eye across the room and they both smiled excitedly.

Lydia: So, we are taking Stiles out tonight to Jungle so we can all show our support since he came out. We are going to be there at 8:30, you need to have Jackson there before us. I am taking Stiles shopping after school so when Jackson sees him tonight, he will be utterly irresistible. 

Danny: Good! Stiles needs a new wardrobe; those comic tees will get him nowhere lol. There is one thing you are forgetting though Lyds, Jackson is Jackson and he will just ignore his crush on Stiles by finding someone else to fuck, how are you going to change that? 

Lydia raised her eyebrow at Danny across the cafeteria and he gave her a questioning glance. 

Lydia: Danny, I think you may have forgotten that I dated Jackson most of my life. I know him quite well. As I know he can be very possessive and very jealous. So, Stiles looking hot af + him dancing very closely with a guy who is hot af = a very jealous Jackson who will be finally be ready to show his true feelings toward Stiles.

Danny: Oh Lydia, you are a queen. Has anyone ever told you that? 

Lydia: Maybe just a few ;)

Lydia and Danny texted throughout the rest of the day talking minor details of the plan. They both were excited about what was to come and the prospect of no longer watching Stiles and Jackson torturing themselves over each other. Lydia may have even enlisted Erika to help her with her Stiles convincing part of the plan. Everything would soon be falling into place.

**Notes for the Chapter:**

> I know we are all highly anticipating the Jungle scene, but I just felt like the boys were going to need a push together and who better to figure that out than Lydia.


	5. Chapter 5

**Summary for the Chapter:**

> First glimpse of the Jungle

Stiles is so excited to get inside to see his friends he doesn’t even notice the familiar Porsche in the parking lot. As he walks into the club Stiles is giddy with the idea that he is here with his friends and for once not alone! He spots his group of friends right away and practically drags Lydia over to them. Stiles, forgetting his new wardrobe, is confused when Scott gawks at him, Isaacs eyebrows raise, Erika gives him a low whistle, and even Aiden gives him an appreciative glance. Boyd just nods his head at him not giving a care in a world about Stiles new appearance, like normal. Stiles feels his face burn a little in embarrassment before taking control of the situation, 

“Yeah, I am hot as hell I get it okay, can we move on now? I though we came here to partayyyy!” 

The group just laughs at Stiles antics and Scott offers to go get everyone some drinks. When Scott leaves the group begins to chat idly about Stiles and Lydia’s shopping trip. What Stiles doesn’t notice is the smirk Lydia gets as she looks across the room at a wide-eyed Jackson who seems to not be able to tear his eyes away from Stiles. 

\------------------------------------------------------------------------------------------------------------------------------------------  
Jackson had been having a good time so far at the club with Danny and Ethan. They got a drink, danced a little, had some good laughs, and he’d even got a couple appreciative glances and given some of his own filing them away for later. What Jackson had not expected to see that night was his actual wet dream walking into the club. 

Jackson’s jaw almost hit the floor when he saw Stiles making his way towards his little group of friends. Stiles was wearing a white v neck that showed off his lean figure. Jackson had always thought Stiles was just skinny, never really looking at him in the locker room unless his feelings be made known, but no Stiles had some muscle and that shirt showed off Stiles so everyone knew he wasn’t just a lanky kid. Jackson looked down seeing how Stiles black skinny jeans hugged his ass perfectly. If that wasn’t bad enough Stiles hair was messed up perfectly to look like he had sex. Ugh how is this fair?! How is Jackson supposed to control himself with Stiles looking utterly delicious? How is he supposed to forget about him for a night when he is so close to him? 

Jackson groans out loud, with a scowl on his face and looks up to meet Danny’s unimpressed gaze. Danny just shakes his head and lets out a laugh,  
“You are so screwed.” Jackson practically growls at the other boy before stating,

“How am I supposed to forget about him when he is right there, looking like that?!” Danny and Ethan both let out a laugh before Ethan says, 

“I don’t mean to cut in or anything, but Jackson it’s so obvious that you like him, and I promise you Danny didn’t tell I figured it out on my own. I mean with how many times I catch you staring at him how was I not supposed to figure it out? Anyways, why do you have to forget about him? Why don’t you just go over there and ask him to dance?” Jackson frowned back at Ethan before stating the obvious, 

“Because Ethan, he’s the only person in the world who isn’t into me. He would never be into me. He would probably just laugh in my face if I asked him to dance.” Ethan gave him a confused look starting to say, 

“What do you mean he isn’t into you, ev---” Danny cuts him off before he could finish, 

“What he means to say is Jackson, you may think Stiles doesn’t like you, but you never know unless you try.” Ethan looked up at Danny question in his eyes as to why Danny cut him off, Danny just returned with an I will tell you later look. Jackson wasn’t convinced though, but those words Danny said were bouncing around in his head. He sighed, 

“I need another drink.” He walked off leaving the other two alone for Danny to share Lydia’s plan with Ethan. 

\------------------------------------------------------------------------------------------------------------------------------------------  
Scott walked back to the group with a tray of shots. Stiles smiled wickedly grabbing his shot, 

“We are going to have so much fun tonight! CHEERS!” Stiles downed his shot. Everyone chorused his cheers and downed theirs as well. The group settled back into excited conversation Stiles was so invested he almost missed a certain greek god named Jackson Whittemore walking towards the bar. Stiles stopped breathing as he took Jackson in, his hair was chopped up in its usual style letting everyone know he’s a badass, his badassery accentuated by his black leather jacket, his blue jeans fit him nicely and showed off his well-toned ass, the shirt Jackson was wearing though almost made Stiles drool. The white shirt hugged Jackson’s chest tightly showing off his muscles, perfectly. 

Lydia, of course, noticed Stiles stop in conversation and followed his eyes to look at the blonde boy. Lydia couldn’t resist anymore, it was time. She was getting Stiles to take some action. She pulled Stiles away from their group of friends and gave Erika a look like she should follow. Stiles was protesting being dragged away from the group, but Lydia didn’t listen. She pulled him until she stopped into a corner in the club so they could talk semi-privately. 

“What the hell was that for?! Why’d you drag me over here?” Stiles practically yelled. Lydia and Erika shared a knowing look and both rolled their eyes at him. Stiles guffawed at them, 

“Seriously, what’s going on?!” Lydia and Erika both just stare at him for a while longer before Erika finally breaks the silence, 

“Stiles we are so tired of this!” Stiles was confused, what had he done? Lydia spoke next acknowledging the confused look on Stiles face, 

“Erika is right Stiles we are so tired of your silent brooding over Jackson, it’s so irritating.” Stiles is awestruck, what the hell? how do they even know he likes Jackson? what is going on? a million questions are flooding his mind. All he can get out is a simple, 

“I don’t know what you are talking about,” he practically whispers. The girls both scoff, 

“So you’re just going to pretend that you don’t practically drool every time you see him,” Lydia offers. 

“Or get lost in thought staring at him across the caf,” Erika states matter-of-factly. Stiles sighs shoulders resigned, damn they know him so well. 

“Okay so what if I do like him it doesn’t mean anything. Jackson could never like me,” Stiles states sadly, with a hint of anger his voice. 

“Wow, boys are so stupid!” Erika and Lydia say in unison. Stiles just looks at them questioningly. Erika starts saying, 

“Stiles, Jackson is majorly crushing on you too! The fact that you two haven’t fucked yet, still amazes me.” Stiles gives her a disbelieving look and opens his mouth to say something before Lydia cuts in, 

“Stiles, she is so right. I would know I dated Jackson for a very long time. I know how he thinks, and I know when he is into someone. I have a plan to get you guys together, tonight!” Stiles can’t find the right words to say as he stares at the two girls in disbelief. So, Lydia just continues on with her plan, 

“So, first we are going to go back to our friends have another drink and we are all going to go dance. Since you are the only one who doesn’t have a mans you are going to find the hottest man in the room, besides Jackson, and you are going to dirty dance with him. Jackson will not be able to control himself any longer and he will cut in and steal you away.  
What do you think?” Stiles gapes at the idea of her plan he’s sure it could work except for the fact that Stiles is Stiles. He says, 

“I have two concerns, the first being how am I going to get the hottest guy in the room to even give me a second glance?” He stopped there because if the girls didn’t have an answer to this they sure wouldn’t be able to help him with his second concern. Erika deadpans a stare at Stiles, 

“Are you kidding me Stilinski? You look sexy as fuck tonight, there is no way in hell this guy will be able to take his eyes off you. As for getting his attention, all you have to do is send him a drink and when he looks up at you bat those eyelashes and tilt your head towards the dance floor where he will undoubtedly meet you.” Wow okay, Stiles was not expecting that, well he could do that. Seems easy enough. 

“Alright,” Stiles states. “That could work. My next concern is what if you guys are wrong and Jackson never cuts in and I got my hopes up all for nothing?” Erika and Lydia give Stiles an understanding look, they had both been in his position before, scared of rejection. Lydia just simply states, 

“You never know unless you try, Stiles.”

**Notes for the Chapter:**

> Ugh I know I am going so slow, its killing me! There's just so much I want to happen. Hope you guys enjoyed this chapter!


	6. Chapter 6

**Summary for the Chapter:**

> Things are moving forward with the plan...

Stiles body was coursing with nerves. He wasn’t sure if he could pull this plan off. Would this work? Does Jackson really have feelings for him? Ugh his brain is going a million miles a minute. 

After some master sleuthing by Erika, Lydia and Stiles, they had found the perfect guy for Stiles to dance with. Honestly, he kind of reminded Stiles of Jackson, and probably been the guy Stiles would have picked to get over Jackson. He was taller than Jackson, his muscles were more prominent than Jackson’s, but he had a sharp jawline and pretty blue eyes. They weren’t bright like Jackson’s though where Stiles could just get lost in the sea of blues that were Jackson’s eyes. Shit he was getting off track he needed to set the plan in motion. 

Stiles walked up to the bar and sent the drink to the second hottest guy in the room. Curious as to where the first is Stiles lets himself look around. He spots Jackson with Danny and Ethan kind of doing their own thing. Stiles lets himself look a little longer, when Jackson turns and catches his eyes, Stiles quickly turns away and focuses back on the plan. When he looks over the waiter had just given #2 the drink from Stiles. He looks up straight at Stiles and winks at him, Stiles gives him a seductive smile and tilts his head toward the dance floor. The other man takes a sip of his drink before nodding and going to meet Stiles on the dance floor. Stiles meets the man half-way before introducing himself, 

“I’m Stiles.” The other man grins, 

“I’m Ryan.” Stiles knew in that moment though that he couldn’t just use the other man, it just isn’t who he is, he had to tell him the truth. 

“Listen Ryan,” Stiles starts. “You are fucking gorgeous like, I can’t even, but I need to tell you the truth. I have a major crush on the brooding blonde over there with the leather jacket and the sharp jawline, well I would like to dance with you and make him jealous... would you be okay with that?” Stiles looks down not really sure what to expect from the other man. What he doesn’t expect is a snort, he looks back up at Ryan. 

“Well, this is unexpected, but I can’t say I’m surprised. Let's see I get to dance with the sexiest guy here and makes someone jealous. Sure, I’ll help you out. Let’s dance!” 

“Thank you!” Stiles lets out a relieved sigh as a flush spreads over his face. He leads Ryan over to his friends and introduces him to them and they all start dancing again. Erika, Lydia, and Stiles all share an excited and hopeful look as they start moving to the music. 

Ryan is a good dancer Stiles will give him that. He’s not one of those guys who just stands there and holds the others waist. Man, Stiles hated those guys. No, Ryan was good. He moves with Stiles, they had some fun and spun each other around, they danced closely and sexily. Stiles is not ashamed to admit he even grinded on him a little, Ryan was helping him, so he wanted to give him the best time. 

\------------------------------------------------------------------------------------------------------------------------------------------   
Jackson had watched Stiles be dragged off by Lydia and Erika and he almost felt sorry for him. Whatever Lydia and Erika wanted; Stiles would have to comply because the two of them always get what they want. Jackson just shook his head and walked back to Danny and Ethan drinks in hand. The three of them just kept laughing, dancing, and occasionally drinking. Jackson would look back over his shoulder ever so often to see if the amber eyed beauty had been let out of the girl's clutches. It had been a couple minutes since the last time Jackson checked, he turned his head and immediately locked eyes with Stiles. Stiles put his head down quickly to try and act like he hadn’t just been caught staring at Jackson. Jackson smirked at the possibility. 

His smirk quickly turned into a frown when he saw where Stiles was looking now. Stiles was headed to the dance floor meeting a man a little taller than Jackson, his muscles were too much for Jackson’s taste, but he kinda reminded Jackson of himself. He had a great jawline and pretty blue eyes just like Jackson. Based on Stiles taste in this guy maybe he had a shot. Jackson couldn’t help the pang of jealousy that went through him when Stiles brought the man over and introduced him to his group of friends. 

When Stiles starts dancing with him Jackson almost loses all semblance of control he has, he can feel it withering away. He feels his frown turn into a scowl. That should be him Stiles is bringing to his friends. That should be him Stiles wants to dance with and have a good time with. Danny interrupts his thoughts with a, 

“What’s wrong Jackson?” Like Danny didn’t know what Stiles dancing with the other guy would be doing to Jackson. Jackson gets out an angry, 

“Danny you know what’s wrong. That should be me!” Danny lets out a little laugh, 

“Well okay then Jackson, go make it you.” Jackson’s scowl deepens if that’s even possible, 

“You know I can’t” Jackson practically growls. Danny lets out an exasperated sigh, 

“Jackson how many times do I have to tell you! You never know unless you try... go get him!” With that statement from Danny and the fact that Stiles is now grinding on this random guy the last of Jackson’s resolve crumbles. He isn’t really sure what has come over him, all he knows is that he needs Stiles. Jackson has no plan in mine he just feels himself walking and getting closer and closer to his destination, Stiles. 

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Stiles was having such a good time dancing with Ryan that he didn’t even notice Jackson coming their way. Jackson walked straight up to Stiles grabbed his wrist and just started pulling him away from the group. Stiles was startled. He looked back to see Lydia stopping a pissed off looking Scott from coming after him. He looked back at Ryan and mouthed him a ‘thank you’, he got a wink in return. Jackson didn’t even stop to talk to Stiles, he just kept dragging him. He pulled him into the bathroom making sure no one else was in there before locking the door. Only after Jackson had the door locked did he let go of Stiles wrist. 

“What the fuck was that Stilinski,” Jackson practically yells. Stiles, feigning ignorance, asks, 

“Whatever do you mean, Jackson? What did I do?” Stiles looks at Jackson batting his eyes. Jackson pushes Stiles up against the bathroom wall until they were mere inches apart. Looking Stiles straight in the eyes he says, 

“You know what you did.” Stiles smirked he had definitely gotten what he’d wanted.

**Notes for the Chapter:**

> Next chapter we will get some of what we have all been waiting for!


	7. Chapter 7

**Summary for the Chapter:**

> It's starting!

Jackson had both of his hands on either side of Stiles head, he was pinned against the wall with Jackson’s mouth within his reach. Stiles wanted to just move in and take what he wanted, but he also knew Jackson. This had to be on his terms, he had to make the decision to move. Stiles moved his eyes up to meet Jackson’s, slowly licking his lips and watching Jackson’s eyes flicker down to watch the movement. Stiles finally responds to Jackson’s earlier statement with a simple, 

“So, what if I do Jackson? What are you going to do about it, huh?” That seemed to be the breaking point for Jackson. Which is exactly what Stiles had wanted when he had said those words. He wanted Jackson to lose all semblance of control and finally just let go. Jackson crashed his lips together with Stiles and they both moaned in relief. Stiles didn’t know if they had kissed for hours or just minutes. Both of them were just lost in the other, doing anything to hear the other make a noise. Licking and biting and sucking, each moaning out their appreciation for what the other was doing to absolutely break them. Stiles was hard, it was becoming so painful he needed some kind of relief. His hips seeming to act on their own accord jutted up to meet Jackson’s. With that the kissing was over as both boys let out a groan of pleasure. Jackson stepped away from Stiles and at first Stiles believed he had ruined everything, but when he looked back into Jackson’s eyes he saw his pupils blown wide and a look that he could only describe as hunger. It made Stiles whimper and just want to fall to the ground and worship the other boy. Which he was about to do until a loud banging came on the door, 

“C’mon dudes there are people who need to go to the bathroom” someone yelled from outside. Both boys seemed to snap out of their fervor and looked slightly embarrassed. They collected themselves and both went to unlock the door and quickly stepped outside it, while the men outside rushed in. Stiles wasn’t sure what to do. He wondered what Jackson was thinking and if a bathroom make out was all it would ever be. Since Jackson wasn’t speaking Stiles figured he had regretted what had just happened and began to move in the direction of his friends. But before he could get too far Jackson reached out and grabbed Stiles hand, 

“Where do you think you’re going?” Stiles whipped around to look at Jackson surprise in his eyes. Stiles stuttered, 

“Well umm... well you didn’t say anything, so I wasn’t sure what you were thinking and I just assumed that maybe you well that was all you wanted and we were umm just going to go different ways and -” Stiles was cut off by Jackson leaning in and kissing him. It wasn’t heated like their first kiss, but just the push of Jackson’s lips against Stiles made Stiles lose all sense of focus. Before Stiles could speak, Jackson pulled back and said, 

“Stiles, now that I have you, I am never going to let you go.” Stiles couldn’t help the huge grin that spread across his face, or the fact that that he was definitely blushing. But when he looked up at Jackson, he could tell that he had a faint blush painted on his face after is admission. Stiles was shocked Jackson so easily told Stiles about his feelings. So, he gave Jackson his cheekiest grin, 

“Well, okay, I guess I’m okay with that.” Jackson grinned at Stiles slightly shaking his head. 

“Well Mr. Whittemore, what’s next?” Stiles looked up at Jackson through his lashes and let his tongue out to wet his lips. “Are we staying or leaving?” Jackson gulped, what had he gotten himself into, who knew Stiles could be so seductive. 

“We are most definitely leaving” Jackson said almost with a growl before grabbing Stiles hand and quickly dragging him out of the club, hiding the huge blush that had spread across his face. 

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Lydia had been so excited when she had seen Jackson storming towards Stiles. She knew that they had broken his resolve to stay away. That he would finally be showing his true feelings to Stiles. What she didn’t expect was a silent Jackson grabbing and pulling Stiles towards the bathroom, but boy was she excited to hear how that went.  
Surprisingly, no one was that shocked when Jackson came and stole Stiles away, not even Ryan. She had stopped Scott from going after them. He was just angry with the way Jackson had come up and man handled Stiles. Which is understandable but damnit Scott those boys need their time alone. She then had turned to Ryan surprised that he wasn’t at all fazed by the sudden loss of his dancing partner. 

“Why are you so calm at the fact that your dancing partner was just whisked away by another man?” She questioned him with a raised eyebrow. Ryan just smirked at her shrugging before explaining, 

“When Stiles asked me to dance, he said he didn’t want to use me and that he actually really liked another guy, and he needed someone to dance with to make him jealous. So, I told him that of course I would help him out. It’s not every day you get someone so honest and not wanting to hurt anyone else to get what they want. I appreciated his honestly.” Lydia just let out a laugh before shaking her head slightly, 

“Well that’s Stiles for you. He is a good guy. Well, Ryan you can hang with us if you want or you can go back with your friends whatever you decide.” Ryan decided to get to know them all a little more before heading back to his friends. Lydia and the gang just kept dancing, but Lydia made sure she always had one eye on the bathroom door. Eventually what seemed like an angry mob had gathered outside the door and only a few seconds later Jackson and Stiles reemerged. Stiles stood there awkwardly for a second before starting back towards their group. Lydia rolled her eyes what was he doing. She was about to go stop him but apparently Jackson was not planning on letting him go. Lydia’s eyes lit up when Jackson gave Stiles a kiss, probably to shut him up. She looked up to make sure Erika had saw, she had. When Lydia saw Jackson start to pull Stiles towards the door she saw hunger in his eyes and she prayed no one got in their way.

**Notes for the Chapter:**

> Hope you enjoy! We are getting closer. I have been trying to post every day, but I want this next chapter to be perfect so I am sorry if it takes me a couple days.


	8. Chapter 8

**Summary for the Chapter:**

> Jackson takes Stiles home

**Notes for the Chapter:**

> I am so sorry this took so long to post. I wanted it to be perfect, but I am still not sure it is. I may have switched a little between Jackson and Stiles pov but I don't think its confusing (I'm sorry if it is). I also had a lot of computer problems, it kept glitching and wouldn't let me type :(

Jackson dragged Stiles to his Porsche not stopping for anyone or anything. There was no way he was going to let anyone stop him from getting what he wanted. Stiles didn’t seem that upset with the fact he was being dragged along. He was actually doing pretty well at keeping up, because Jackson didn’t feel any resistance. His mind was already swimming with all of the possibilities Stiles, and he had open to them. He didn’t know what would come of this night all he knew is what he needed here and now. That was Stiles. 

Ever since he saw Stiles dancing with that other guy in the club earlier, he has had a one-track mind. He finally had the confidence he needed to go after what he wanted, by confidence he means alcohol + jealousy. It all worked out in the end because Stiles seemed to be on the same page as Jackson. He even seemed to be goading him a bit. Maybe Stiles was just trying to make Jackson jealous by dancing with that guy right in his line of sight, that would make sense. Jackson didn’t know what he planned to do with Stiles right now, just because he had been in love with him for as long as he could remember that doesn’t mean the other boy knew his feelings. Jackson doesn’t want Stiles to think he is only using him for his body or something like that. Jackson drove on autopilot to his house, determined to have a talk with Stiles and laying it all out for Stiles to take it or leave it. 

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Stiles was having the biggest rush of his life since Jackson dragged him off the dance floor. His mind could barely settle around the fact that Jackson had kissed him in that bathroom and then had kept him from leaving. The next thing Stiles knew he was being dragged to Jackson’s Porsche, hmmmm how had he not noticed that was there when he walked in. He was silent in the car with Jackson, he wasn’t sure what to do or say, he didn’t want to ruin the mood. Plus, the other boy seemed to be lost in his own thoughts. Maybe he was already regretting his choice to pull Stiles out of that club. Stiles hoped that wasn’t true. Honestly, if he could have just one night with Jackson, he would take it over not having anything at all. 

When Jackson pulled up to the “Whittemore Mansion” Stiles wasn’t surprised. He had figured that they would go somewhere Jackson was familiar with. Stiles stayed quiet and didn’t hesitate to get out of the car. Jackson stayed silent also, but slowly made his way to his front door being sure to not leave Stiles behind. When they got inside, instead of going upstairs like Stiles thought they would Jackson led Stiles to a couch in his living room. Jackson was still silent, sitting at the couch and Stiles was starting to lose his patience. He had to do something his brain wouldn’t just let him sit there and not say anything, so he went to his first line of defense, humor. 

“So Jax,” Stiles started the nickname slipping out easily. “Did you bring me here to kill me or what? Because this silence might actually do it if that wasn’t your plan already,” Stiles giggled. Jackson looked startled by the Stiles breaking the silence and just stared at the other boy seemingly trying not find something to say by the way his face was scrunched up. Stiles wasn’t sure what to do with the exaggerated silence that followed his question so he put two and two together and figured that Jackson was just trying to let him down easy, he had changed his mind on the way home from the club. So, Stiles stood up, 

“Listen Jackson I think I get it. It’s okay, you don’t have to worry about letting me down easy or anything. I will just go. No hard feelings, okay?” Stiles turned and started to walk towards the door. He didn’t hear Jackson get up so when he grabbed his hand and spun him around into the door, he was a bit surprised. He gasped when his back was against the door, remembering the similar position they were in earlier. Jackson looked up to meet Stiles eyes and he finally let everything he felt come out, 

“Stiles, please, I’m sorry. I’m only silent because I am just trying to find the right way to tell you that I’m in love with you, okay? I love how you are easily the smartest person in the room, but a lot of people don’t see that because you cover it with sarcasm and humor. I love how your laugh can fill a whole room and make anyone laugh along with you. I even love your horrible fashion taste with your comic tees.” Stiles just stood there his mouth slightly agape taking in everything Jackson had just admitted to him. His mind was racing he could not believe Jackson loved him back. Never in his wildest dreams did he think that would happen. He almost forgot that he had to respond until he felt Jackson take a step back and saw the pained expression on his face. Stiles stopped him grabbing his bicep, 

“Jackson Whittemore, you rendered me utterly speechless which everyone knows is a difficult feat because my mouth goes about a million miles a minute. I never believed that you could feel the same way about me that I do about you.” Stiles reached his hand up cupping Jackson’s face. “I love you too and--” Stiles didn’t get to finish what he was saying because Jackson surged forward and covered his mouth with Jackson’s own. That broke the spell and Jackson and Stiles were making out passionately. Jackson was getting as close to Stiles as he could making sure every inch of their bodies that could were touching. Jackson’s hands were running all over Stiles body like he was trying to memorize the feel of every inch. Everywhere his hand went left a trail of goosebumps on Stiles skin. 

Stiles wanted more, he whined into Jacksons mouth and bucked his hips up to meet Jackson’s. This time the spell they were under wasn’t broken. Jackson lifted Stiles up and Stiles tied his legs behind Jacksons back while Jackson carried him to his room. Jackson had to break their kiss to walk up the stairs, though Stiles was disappointed, he decided there were other things he could do while Jackson had to focus. Stiles kissed down Jackson’s jaw to his neck marking it so everyone would know Jackson was his. Jackson paused and groaned when Stiles started kissing his neck. When Stiles was satisfied with the mark he left on Jackson Stiles moved up to whisper in Jackson’s ear, 

“Jax, you better hurry up and make it your bedroom because if you don’t get there quick, we are just going to have to finish right here because I can’t wait much longer.” Stiles lightly bit on Jackson’s earlobe when he was finished speaking and Jackson outright moaned loudly. Stiles smirked at the sounds he could pull from Jackson. But Jackson got the message and started moving faster. He made it to his room quickly and threw Stiles onto his bed. 

Jackson stood slowly taking his shirt off. Stiles couldn’t help but stare as Jackson's muscles flexed while lifting the shirt over his head. Jackon moved to begin taking off his pants and glanced at Stiles who was unmoved. Jackson smirked back at Stiles whose mouth was slightly agape, but his eyes looked like he was in a trance. 

“You’re the one who said they wanted to get this show on the road and now you aren’t even moving.” Jackson laughed. That snapped Stiles back into focus, he quickly stripped off his shirt and pants, but left his underwear on feeling slightly self-conscious. Now it was Jacksons turn to stare. He didn’t get lost for too long though, because his cock was straining hard against his boxers and it reminded him of the prize he needed to claim. He moved over to the bed climbed on top of Stiles, holding himself up on his forearms before leaning in and kissing Stiles hard. The kiss was messy and heated and both still in their underwear were looking for any kind of friction rubbing up on each other. Jackson moved his lips down marking a spot on Stiles neck just as the other boy had done to him earlier. Stiles moaned an appreciative groan but it eventually turned into a whine. 

“Please Jackson” Stiles whined bucking his hips. He wasn’t really sure what he was asking for, but it seemed that Jackson understood what he was asking. Jackson kissed down Stiles body, making his way down to Stiles waist, he lightly traced the top of Stiles underwear before pulling them off. Jackson stared a little at Stiles cock, he’s not sure what he was expecting but it definitely wasn’t this, Stiles cock was big it was roughly 8 inches and fairly thick. It was beautiful. Jackson swiftly took Stiles into his mouth. Taking the other teen as far as he could go while keeping his other hand at the base in perfect timing as his mouth as he moved up in down. When he reached the top of Stiles dick he pulled off to kitten lick at the slit tasting Stiles salty precum. 

Stiles was loving the feel of Jackson’s mouth on his dick. He couldn’t help the moans and groans and occasional ‘fucks’ that escaped his mouth. They only seemed to spur Jackson on. Stiles had his hand in Jackson’s hair pulling slightly, from the groan Jackson gave Stiles knew he needed to file that piece of information away for later. Stiles was about to lose it, he started to pull Jackson’s head off and barely had time for a warning, 

“Jax I’m gonna---” was all Stiles got out before he was erupting. Jackson had pulled his mouth as far as he could go on Stiles dick, swallowing all the cum his lover had just given to him. 

“Oh my gosh that was so hot, I can’t even right now” Stiles breathed out coming down from the high of his orgasm. He pulled Jackson up for a kiss, tasting himself. He pulled away looked Jackson straight in the eye and said, 

“If you don’t fuck me right now I’m leaving” Stiles didn’t actually think he would leave Jackson with blue balls but he had to give the other boy incentive to finally get inside him. When Stiles said those words Jackson could have erupted right there and Stiles saw it in his eyes. Jackson reached his finger up to Stiles mouth for him to suck on, which he did enthusiastically. When Jackson was satisfied he brought his finger down and circled at Stiles entrance. Right when it looked like Stiles was about to say something Jackson pushed his finger inside Stiles. Stiles moaned outright and it only spurred Jackson on. Jackson moved his finger in and out of Stiles searching for his sweet spot. Pretty soon he added another finger and then a third pumping it in and out of Stiles, when he crooked them just a little he finally hit that bundle of nerves inside the other boy. Stiles threw his head back against the bed nearly screaming. Good thing Jacksons parents were not home this weekend, Jackson thought to himself. Stiles was already fully hard again and Jackson knew it was time. Jackson slid off his boxers and looked down at his neglected dick. It was and angry red. He could feel Stiles eyes on him as he used his precum to slather up his cock.   
When Stiles saw Jackson’s dick he couldn’t wait to get it inside of him. Jackson’s dick was a little shorter than his maybe 7 inches, but it was thicker than Stiles. He was a little worried about how it would fit inside him, he had never had someone like Jackson before. But the excitement of having Jackson finally inside him outweighed the nerves. He watched hungrily as Jackson lubed up his cock with the precum he was producing. Stiles laid his head back on the bed as he felt Jackson line up against his rim. Stiles started to try and relax his whole body so there wouldn’t be any resistance when Jackson entered him. Stiles groaned in pleasure as Jackson slowly pushed inside of him. When Jackson all the way in Stiles felt so full and it was amazing. 

As soon as Jackson entered Stiles he was afraid to move. Stiles was so tight, and it felt so good, he had to take a second so he wouldn’t cum right then in there. Jackson was snapped out of his fight for control by Stiles pushing back on his dick and begging, 

“Jackson, please, I need you to fuck me. Fuck me so I can’t walk tomorrow.” That really snapped Jackson back into reality. He wasn’t going to let Stiles down. He slowly pulled his dick out until it was just the head in and he heard Stiles whine from the loss, but he quickly slammed back into Stiles getting an appreciative groan. He kept the pace hard and fast. He felt himself getting close so he changed the angle so he could hit Stiles prostate every time. Stiles was writhing and pleading underneath him. Jackson was ready to give him what he wanted. Jackson reached up and gave Stiles dick two quick jerks before he was cumming. The spasm of Stiles hole on Jackson’s dick made Jackson cum with Stiles name on his tongue. He slowly pulled out of Stiles and saw Stiles make a face at the loss. That was the best sex he had ever had, and from the look of pure bliss on Stiles face he was sure that it was the same for him. 

Stiles could barely think. That was the best sex he had had in his life, granted he had only had sex two times before this but still. He could feel himself already starting to drift off. Jackson had laid down beside him and was already pulling him into his arms. They drifted off into peaceful slumbers, both happy they had finally gotten the person they love. 

The next morning Stiles woke up before Jackson and went searching for his phone, there was someone he needed to thank. Stiles found his phone and quickly texted Lydia. 

Stiles: Thank you for everything. 

Lydia: Yay! I’m so happy! I am just so glad you went along with my plan. 

Stiles: You never know unless you try, right? ;)

**Notes for the Chapter:**

> Thank you for reading! I really hope you enjoyed this story. I would love to hear your thoughts on it. Please stay safe out there with COVID-19 on the loose. I love you all! Thank you for taking this journey with me as I wrote my first fic. :)

**Author's Note:**

> This is my first try at writing a fic! I am not really sure how long this will be I had an idea and wanted to write it. Please let me know in the comments what you think it will be greatly appreciated! Thank you :)


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